Synthesis and characterization of soluble low-bandgap oligothiophene-[all]-S,S-dioxides-based conjugated oligomers and polymers

Authors

  • Elizabeth Amir,

    1. Materials Research Laboratory, University of California, Santa Barbara, California 93106-9510
    2. Mitsubishi Chemical Center for Advanced Materials, University of California, Santa Barbara, California 93106-9510
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  • Kulandaivelu Sivanandan,

    1. Materials Research Laboratory, University of California, Santa Barbara, California 93106-9510
    2. Mitsubishi Chemical Center for Advanced Materials, University of California, Santa Barbara, California 93106-9510
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  • Justin E. Cochran,

    1. Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510
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  • John J. Cowart,

    1. Mitsubishi Chemical Center for Advanced Materials, University of California, Santa Barbara, California 93106-9510
    2. Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510
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  • Sung-Yu Ku,

    1. Materials Research Laboratory, University of California, Santa Barbara, California 93106-9510
    2. Mitsubishi Chemical Center for Advanced Materials, University of California, Santa Barbara, California 93106-9510
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  • Jung Hwa Seo,

    1. Materials Department, University of California, Santa Barbara, California 93106-9510
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  • Michael L. Chabinyc,

    1. Materials Research Laboratory, University of California, Santa Barbara, California 93106-9510
    2. Mitsubishi Chemical Center for Advanced Materials, University of California, Santa Barbara, California 93106-9510
    3. Materials Department, University of California, Santa Barbara, California 93106-9510
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  • Craig J. Hawker

    Corresponding author
    1. Materials Research Laboratory, University of California, Santa Barbara, California 93106-9510
    2. Mitsubishi Chemical Center for Advanced Materials, University of California, Santa Barbara, California 93106-9510
    3. Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510
    4. Materials Department, University of California, Santa Barbara, California 93106-9510
    • Materials Research Laboratory, University of California Santa Barbara, California 93106-9510
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Abstract

The synthesis and characterization of a new family of soluble oligothiophene-S,S-dioxides and their use as building blocks to form polythiophene-S,S-dioxides via microwave-assisted Stille coupling polymerization are described. Incorporation of the sulfone group into the polythiophene backbone leads to narrowing of the polymer bandgap, and while the energies of both Frontier orbitals in polythiophene-S,S-dioxide are lower with respect to polythiophenes, this tendency is considerably stronger for the lowest unoccupied molecular orbital than for the highest occupied molecular orbital, resulting in greater electron-accepting ability. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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